Benzisothiazolazo, diaminopyridine dyes

ABSTRACT

A compound having the formula: ##STR1## where X is hydrogen, chlorine or bromine, B is hydrogen, methyl, ethyl or propyl, and one of the radicals R 1  or R 2  is phenyl which is unsubtituted or mono- or poly-substituted by chlorine, methyl, ethyl, t-butyl, phenoxy, methoxy, ethoxy, propoxy or butoxy, and the other is C 2  -C 8  -alkyl which is unsubstituted or substituted by C 1  -C 8  -alkoxy or phenyl, or is allyl, cyclopentyl, cyclohexyl, methylcyclohexyl, ##STR2## The compounds of formula (I) are used as dyes, preferably for cellulose and cellulose-containing fabrics.

This application is a continuation of application Ser. No. 454,246, filed Dec. 29, 1982, now abandoned.

SUMMARY OF THE INVENTION

Azo dye having either 2-arylamino-5-cyano-6-alkylamino- or 2-alkylamino-5-cyano-6-arylamino-pyridine as coupling component general formula I ##STR3## where X is hydrogen, chlorine or bromine, B is hydrogen, methyl, ethyl or propyl, and one of the radicals R¹ or R² is phenyl which is unsubstituted or mono- or poly-substituted by chlorine, methyl, ethyl, t-butyl, phenoxy, methoxy, ethoxy, propoxy or butoxy, and the other is C₂ -C₈ -alkyl which is unsubstituted or substituted by C₁ -C₈ -alkoxy or phenyl, or is allyl, cyclopentyl, cyclohexyl, methylcyclohexyl, ##STR4##

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

Specific examples of alkyl radicals R¹ and R² are C₂ H₅, n--C₃ H₇, i--C₃ H₇, n-- or i--C₄ H₉, n-- or i--C₅ H₁₁, n-- or i--C₆ H₁₃, n-- or i--C₇ H₁₅, n-- or i--C₈ H₁₇, C₂ H₄ OCH₃, C₂ H₄ OC₂ H₅, C₂ H₄ OC₃ H₇, C₂ H₄ OC₄ H₉, (CH₂)₃ OCH₃, C₂ H₄ OCH(CH₃)₂, (CH₂)₃ OC₂ H₅, (CH₂)₃ OC₃ H₇, (CH₂)₃ OC₄ H₉, (CH₂)₃ OC₆ H₁₃, (CH₂)₃ OC₈ H₁₇, ##STR5##

The compounds of the formula I can be prepared by reacting a diazo compound of an amine of the formula ##STR6## with a coupling component of the formula ##STR7## in a conventional manner. Details may be found in the Examples, in which parts and percentages, unless indicated otherwise, are by weight.

The compounds of the formula I are preferably used for fixative printing (known under the tradename DYBLN, cf. eg. German Pat. No. 1,811,796 or U.S. Pat. No. 3,706,525), in which tone-on-tone dyeings can be produced on mixtures of cellulose fibers and polyester. Blue to black dyeings with very good fastness characteristics in comparison with conventional dyes, in particular lightfastness and wetfastness, and also a high stability to live steam, are obtained.

Particularly important compounds are those of the formula I a ##STR8## where R¹ and R² have the above meanings, but R² is preferably ##STR9## and R¹ is preferably ##STR10## always in combination with an unsubstituted or substituted alkyl radical of the type defined, and alkyl is methyl, ethyl or t-butyl.

Examples of preferred unsubstituted or substituted radicals R¹ and R² are --CH(CH₃)₂, ##STR11##

Combinations where R¹ is C₆ H₅ and R² is ##STR12## are also preferred.

EXAMPLE 1

19.6 parts of the diazo component of the formula ##STR13## are prepared and diazotized with nitrosylsulfuric acid, by the process described in German Pat. No. 2,412,975. The finished diazonium salt solution is then run into a suspension of 31.1 parts of the coupling component of the formula ##STR14## in a mixture of 400 parts of water and 900 parts of ice. About 30% strength sodium formate solution is added to the coupling mixture, until the pH of the suspension has risen to 0.3-0.7, during which time the temperature is kept at below +5° C. by addition of ice. The coupling has ended after about 30 minutes, and the precipitated dye is isolated, washed salt-free and dried, in a conventional manner. 49 parts of a bluish black powder of the formula ##STR15## are obtained. The dye melts at from 225° C. to 230° C. and dyes cotton, polyester and polyester/cotton union fabric in lightfast reddish blue to navy shades.

If, instead of the above coupling component, the coupling component mixture formed when 2,6-dichloro-3-cyano-4-methylpyridine is reacted first with 2-methoxyethylamine and then with 2-methoxyaniline, as described in German Pat. No. 2,260,827, is used, the corresponding amount of a dye mixture is obtained which, in addition to the above dye, contains a minor amount of the dye of the formula ##STR16## The mixture melts at from 185° to 229° C.,

The absorption maximum of a solution of the dye in dimethylformamide (about 10 mg/l) is 589.5 nm.

The dye mixture dyes or prints cotton, polyester and polyester/cotton union fabric in highly lightfast clear blue to navy hues at a slightly lower temperature than the pure dyes. The dyeings or prints have good wetfastness, even when the hues are deep, and they are also stable to hot steam.

An example of a suitable dyeing method is the procedure described in European Pat. No. 0,012,935, and an example of a suitable printing method is that of German Pat. No. 1,811,796.

EXAMPLE 2

27.5 parts of the diazo component of the formula ##STR17## are stirred into 200 parts of 96-98% strength sulfuric acid at from 10° to 15° C. The mixture is then cooled to 0°-10° C., and a mixture of 100 parts by volume of glacial acetic acid and 17 parts of propionic acid is added dropwise at this temperature. 33 parts of 42-44% strength nitrosylsulfuric acid solution is then added dropwise at 0°-4° C. in the course of from 20 to 30 minutes, with cooling. The diazotization mixture is subsequently stirred at from 0° to 4° C. for from 31/2 to 4 hours, and is then run, with stirring, into a suspension of 31.1 parts of the mixture of coupling components of the formulae ##STR18## which is described in Example 1, in a mixture of 400 parts of water and 900 parts of ice.

After the diazonium salt solution has been added, the pH of the coupling mixture is increased to 0.5-10 with approximately 30% strength sodium formate solution, during which the temperature is kept at from -3° to +5° C. by addition of ice.

The reacted coupling mixture is heated to 85° C. with steam and is kept at from 85° to 95° C. for 15-30 minutes, and the precipitated dye is washed salt-free in a conventional manner and dried to give 57 parts of a black powder of the formulae ##STR19## The mixing ratio of the dyes is the same as that of the coupling components used.

The dye mixture is soluble in dimethylformamide, giving a blue solution, and dyes or prints cotton, polyester or polyester/cotton union fabric in blue to navy hues. The resulting dyeings or prints have good lightfastness and wetfastness.

EXAMPLE 3

19.6 parts of the diazo component of the formula ##STR20## are prepared and diazotized by the process described in German Pat. No. 2,412,975. The diazonium salt solution is then run into a suspension of a mixture of 20.6 parts of the coupling component of the formula ##STR21## and 9.8 parts of the coupling component of the formula ##STR22## (which, because of the method of synthesis, each contain a relatively small amount of the 2,6-isomeric coupling component) in a mixture of 400 parts of water and 900 parts of ice. The individual coupling components are prepared from 2,6-dichloro-3-cyano-4-methylpyridine by a method similar to that described in German Pat. No. 2,260,827, by reacting the heterocyclic compound first with the aliphatic amine and then, in a second step, with the aromatic amine.

The coupling is brought to completion by a procedure similar to that described in Example 1, and the dye is worked up in a conventional manner. 47.5 parts of dye powder are isolated. A dye mixture is obtained, containing individual components of the formulae ##STR23## and relatively small amounts of ##STR24##

The dye mixture melts in the range from 185° to 198° C. and its powder is bluish black and dissolves in dimethylformamide giving a blue solution.

Pale dyeings or prints on polyester, cotton or polyester/cotton union fabrics are reddish blue, whilst deeper dyeings are clear navy.

The dye mixture dyes polyester and cotton with a good matching of hue. The dyeings have good fastness characteristics in use.

The dyes listed in the Tables can be prepared by a procedure similar to that described in the Examples. Where two hues are given for dyeings or prints, the first refers to a lighter dyeing (or print) using about 0.2-0.4% of dye, and the second refers to a dyeing (or print) using not less than 0.8% of dye.

                                      TABLE 1                                      __________________________________________________________________________      ##STR25##                                                                     No. R.sup.1       R.sup.2        R.sup.3                                                                            Hue                                       __________________________________________________________________________      4                                                                                  ##STR26##    C.sub.6 H.sub.5                                                                               CH.sub.3                                                                           reddish blue navy                          5                                                                                  ##STR27##    "              "   "                                          6                                                                                  ##STR28##    "              "   "                                          7                                                                                  ##STR29##    "              "   "                                          8  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                             "              "   "                                          9                                                                                  ##STR30##    "              "   "                                         10  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)                                                         "              "   "                                         11  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)                                                         "              "   "                                         12                                                                                  ##STR31##    "              "   "                                         13  C.sub.3 H.sub.6 OCH.sub.3                                                                    "              "   "                                         14  C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                             "              "   "                                         15                                                                                  ##STR32##    "              "   "                                         16                                                                                  ##STR33##    "              "   "                                         17                                                                                  ##STR34##    "              "   "                                         18                                                                                  ##STR35##                                                                                    ##STR36##     "   "                                         19                                                                                  ##STR37##    "              "   "                                         20                                                                                  ##STR38##    "              "   "                                         21                                                                                  ##STR39##    "              "   "                                         22  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                             "              "   "                                         23  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)                                                         "              "   "                                         24  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)                                                         "              "   "                                         25                                                                                  ##STR40##    "              "   "                                         26  C.sub.3 H.sub.6 OCH.sub.3                                                                    "              "   blue navy                                 27  C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                             "              "   "                                         28                                                                                  ##STR41##    "              "   "                                         29                                                                                  ##STR42##                                                                                    ##STR43##     "   "                                         30  C.sub.2 H.sub.4 OCH.sub.3                                                                    "              "   "                                         31  C.sub.3 H.sub.6 OCH.sub.3                                                                    "              "   "                                         32                                                                                  ##STR44##    CH.sub.2 CHCH.sub.2                                                                           "   "                                         33                                                                                  ##STR45##                                                                                    ##STR46##     "   "                                         34                                                                                  ##STR47##                                                                 35                                                                                  ##STR48##    "              "   "                                         36                                                                                  ##STR49##    "              "   "                                         37  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                             "              "   "                                         38  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)                                                         "              "   "                                         39  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)                                                         "              "   "                                         40  C.sub.3 H.sub.6 OCH.sub.3                                                                    "              "   "                                         41  C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                             "              "   "                                         42                                                                                  ##STR50##    "              "   "                                         43  C.sub.3 H.sub.6 OCH.sub.3                                                                     ##STR51##     "   dull blue bluish black                    44                                                                                  ##STR52##    "              "   "                                         45                                                                                  ##STR53##    "              "   "                                         46                                                                                  ##STR54##                                                                                    ##STR55##     "   greenish blue bluish black                47                                                                                  ##STR56##    "              "   "                                         48                                                                                  ##STR57##    "              "   "                                         49                                                                                  ##STR58##    "              "   "                                         50  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                             "              "   "                                         51                                                                                  ##STR59##    "              "   "                                         52  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)                                                         "              "   "                                         53  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)                                                         "              "   "                                         54                                                                                  ##STR60##    "              "   "                                         55  C.sub.3 H.sub.6 OCH.sub.3                                                                    "              "   "                                         56  C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                             "              "   "                                         57  CH.sub.2 CH.sub.2 OCH.sub.3                                                                  "              "   dull blue bluish black                    58  C.sub.3 H.sub.6 OCH.sub.3                                                                    "              H   "                                         59                                                                                  ##STR61##                                                                                    ##STR62##     CH.sub.3                                                                           "                                         60                                                                                  ##STR63##    "              "   "                                         61                                                                                  ##STR64##    "              "   "                                         62                                                                                  ##STR65##    "              "   "                                         63  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                             "              "   "                                         64  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)                                                         "              "   "                                         65  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)                                                         "              "   "                                         66                                                                                  ##STR66##    "              "   "                                         67  C.sub.3 H.sub.6 OCH.sub.3                                                                    "              "   "                                         68  C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                             "              "   "                                         69  C.sub.2 H.sub.4 OCH.sub.3                                                                    "              "   "                                         70  C.sub.3 H.sub.6 OCH.sub.3                                                                    "              H   "                                         71  "             "              C.sub.2 H.sub.5                                                                    "                                         72  C.sub.4 H.sub.9 (n)                                                                          "              CH.sub.3                                                                           "                                         73  C.sub.3 H.sub.6 OCH.sub. 3                                                                    ##STR67##     "   "                                         74                                                                                  ##STR68##                                                                                    ##STR69##     "   bluish grey coal black                    75                                                                                  ##STR70##    "              "   "                                         76                                                                                  ##STR71##    "              "   "                                         77                                                                                  ##STR72##    "              "   "                                         78  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                             "              "   "                                         79  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)                                                         "              "   "                                         80  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)                                                         "              "   "                                         81                                                                                  ##STR73##    "              "   "                                         82  C.sub.3 H.sub.6 OCH.sub.3                                                                    "              "   "                                         83  C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                             "              "   "                                         84                                                                                  ##STR74##                                                                 85                                                                                  ##STR75##    "              "   "                                         86                                                                                  ##STR76##    "              "   "                                         87  C.sub.2 H.sub.4 OCH.sub.3                                                                    "              "   "                                         88  C.sub.3 H.sub.6 OCH(CH.sub.3).sub.2                                                          "              "   "                                         89  C.sub.3 H.sub.6 OC.sub.8 H.sub.17 (i)                                                        "              "   "                                         90  C.sub.3 H.sub.6 OCH.sub.3                                                                    "              H   "                                         91  "             "              C.sub.2 H.sub.5                                                                    "                                         92  C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                             "              H   "                                         93                                                                                  ##STR77##                                                                                    ##STR78##     CH.sub.3                                                                           dull blue coal black                      94                                                                                  ##STR79##    "              "   "                                         95                                                                                  ##STR80##    "              "   "                                         96                                                                                  ##STR81##    "              "   "                                         97  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                             "              "   "                                         98                                                                                  ##STR82##    "              "   "                                         99  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)                                                         "              "   "                                         100 C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)                                                         "              "   "                                         101                                                                                 ##STR83##    "              "   "                                         102 C.sub.3 H.sub.6 OCH.sub.3                                                                    "              "   "                                         103 C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                             "              "   "                                         104                                                                                 ##STR84##    "              "   "                                         105                                                                                 ##STR85##    "              "   "                                         106                                                                                 ##STR86##    "              "   "                                         107 C.sub.2 H.sub.4 OCH.sub.3                                                                    "              "   "                                         108 C.sub.3 H.sub.6 OCH.sub.3                                                                     ##STR87##     "   bluish grey coal black                    __________________________________________________________________________

                  TABLE 2                                                          ______________________________________                                          ##STR88##                                                                     No.  R.sup.1        R.sup.2       R.sup.3                                                                            Hue                                      ______________________________________                                         109                                                                                  ##STR89##                                                                                     ##STR90##    H   blue navy                                110                                                                                  ##STR91##     "             "   blue navy                                111                                                                                  ##STR92##     "             "   blue navy                                112                                                                                  ##STR93##     "             "   blue navy                                113  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                              "             "   blue                                                                           navy                                     114                                                                                  ##STR94##     "             "   blue navy                                115  CH.sub.2 CH.sub.2C.sub.6 H.sub.5                                                              "             "   blue                                                                           navy                                     116                                                                                  ##STR95##     "             "   blue navy                                117  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)                                                          "             "   blue                                                                           navy                                     118  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (i)                                                           ##STR96##    H   blue navy                                119  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)                                                          "             "   blue                                                                           navy                                     120  C.sub.3 H.sub.6 OCH.sub.3                                                                     "             "   blue                                                                           navy                                     121  C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                              "             "   blue                                                                           navy                                     122  C.sub.3 H.sub.6 OC.sub.3 H.sub.7 (n)                                                          "             "   blue                                                                           navy                                     123  C.sub.3 H.sub.6 OC.sub.8 H.sub.17 (i)                                                         "             "   blue                                                                           navy                                     124                                                                                  ##STR97##     "             "   blue navy                                125                                                                                  ##STR98##     "             Cl  blue navy                                126                                                                                  ##STR99##                                                                                     ##STR100##   H   blue navy                                127                                                                                  ##STR101##    "             Cl  blue                                     128                                                                                  ##STR102##    "             "    "                                       129                                                                                  ##STR103##    "             "    "                                       130  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                               ##STR104##   H   blue navy                                131  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)                                                          "             "   blue                                                                           navy                                     132  C.sub.2 H.sub.4 OC.sub.2 H.sub.7 (i)                                                          "             "   blue                                                                           navy                                     133  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)                                                          "             "   blue                                                                           navy                                     134  C.sub.3 H.sub.6 OCH.sub.3                                                                     "             "   blue                                                                           navy                                     135  C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                              "             "   blue                                                                           navy                                     136  C.sub.3 H.sub.6 OC.sub.3 H.sub.7 (n)                                                          "             "   blue                                                                           navy                                     137  C.sub.3 H.sub.6 OC.sub.8 H.sub.17 (i)                                                         "             "   blue                                                                           navy                                     138                                                                                  ##STR105##                                                                                    ##STR106##   "   navy bluish black                        139                                                                                  ##STR107##    "             "   navy  bluish black                       140                                                                                  ##STR108##    "             "   navy bluish black                        141                                                                                  ##STR109##    "             "   navy bluish black                        142  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                              "             "   navy                                                                           bluish                                                                         black                                    143  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)                                                           ##STR110##   H   navy bluish black                        144  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (i)                                                          "             "   navy                                                                           bluish                                                                         black                                    145  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)                                                          "             "   navy                                                                           bluish                                                                         black                                    146  C.sub.3 H.sub.6 OCH.sub.3                                                                     "             "   navy                                                                           bluish                                                                         black                                    147  C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                              "             "   navy                                                                           bluish                                                                         black                                    148  C.sub.3 H.sub.6 OC.sub.3 H.sub.7 (n)                                                          "             "   navy                                                                           bluish                                                                         black                                    149  CH(CH.sub.3).sub.2                                                                            "             "   blue                                                                           navy                                     150                                                                                  ##STR111##                                                                                    ##STR112##   H   blue navy                                151                                                                                  ##STR113##    "             "   blue navy                                152                                                                                  ##STR114##    "             "   blue navy                                153                                                                                  ##STR115##    "             "   blue navy                                154  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                              "             "   blue                                                                           navy                                     155  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)                                                          "             "   blue                                                                           navy                                     156  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (i)                                                           ##STR116##   H   blue navy                                157  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)                                                          "             "   blue                                                                           navy                                     158  C.sub.3 H.sub.6 OCH.sub.3                                                                     "             "   blue                                                                           navy                                     159  C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                              "             "   blue                                                                           navy                                     160  C.sub.3 H.sub.6 OC.sub.3 H.sub.7 (n)                                                          "             "   blue                                                                           navy                                     161  C.sub.3 H.sub.6 OC.sub.8 H.sub.17 (i)                                                         "             "   blue                                                                           navy                                     162                                                                                  ##STR117##                                                                                    ##STR118##   "   navy                                     163                                                                                  ##STR119##    "             "    "                                       164                                                                                  ##STR120##                                                                                    ##STR121##   "   greenish  blue navy                      165                                                                                  ##STR122##    "             "   greenish blue navy                       166                                                                                  ##STR123##    "             "   greenish blue navy                       167                                                                                  ##STR124##    "             "   greenish blue navy                       168  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                              "             "   greenish                                                                       blue                                                                           navy                                     169                                                                                  ##STR125##                                                                                    ##STR126##   H   greenish blue navy                       170  CH.sub.2 CH.sub.2C.sub.6 H.sub.5                                                              "             "   greenish                                                                       blue                                                                           navy                                     171                                                                                  ##STR127##    "             "   greenish blue navy                       172  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)                                                          "             "   greenish                                                                       blue                                                                           navy                                     173  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (i)                                                          "             "   greenish                                                                       blue                                                                           navy                                     174  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)                                                          "             "   greenish                                                                       blue                                                                           navy                                     175  C.sub.3 H.sub.6 OCH.sub.3                                                                     "             "   greenish                                                                       blue                                                                           navy                                     176  C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                              "             "   greenish                                                                       blue                                                                           navy                                     177  C.sub.3 H.sub.6 OC.sub.3 H.sub.7 (n)                                                          "             "   greenish                                                                       blue                                                                           navy                                     178  C.sub.3 H.sub.6 OC.sub.8 H.sub.17 (i)                                                         "             "   greenish                                                                       blue                                                                           navy                                     179                                                                                  ##STR128##    "             "   greenish blue navy                       180  C.sub.2 H.sub.4 OCH.sub.3                                                                     "             "   greenish                                                                       blue                                                                           navy                                     181                                                                                  ##STR129##                                                                                    ##STR130##   "   blue navy                                182                                                                                  ##STR131##    "             "   blue navy                                183                                                                                  ##STR132##                                                                                    ##STR133##   H   blue navy                                184                                                                                  ##STR134##    "             "   blue navy                                185  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                              "             "   blue                                                                           navy                                     186  CH.sub.2 CH.sub.2C.sub.6 H.sub.5                                                              "             "   blue                                                                           navy                                     187                                                                                  ##STR135##    "             "   blue navy                                188  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)                                                          "             "   blue                                                                           navy                                     189  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (i)                                                          "             "   blue                                                                           navy                                     190  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)                                                          "             "   blue                                                                           navy                                     191  C.sub.3 H.sub.6 OCH.sub.3                                                                     "             "   blue                                                                           navy                                     192  C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                              "             "   blue                                                                           navy                                     193  C.sub.3 H.sub.6 OC.sub.3 H.sub.7 (n)                                                          "             "   blue                                                                           navy                                     194  C.sub.3 H.sub.6 OC.sub.8 H.sub.17 (i)                                                         "             "   blue                                                                           navy                                     195                                                                                  ##STR136##    "             "   blue navy                                196  C.sub.2 H.sub.4 OCH.sub.3                                                                     "             "   blue                                                                           navy                                     197                                                                                  ##STR137##                                                                                    ##STR138##   H   blue navy                                198                                                                                  ##STR139##                                                                                    ##STR140##   "   blue navy                                199                                                                                  ##STR141##    "             "   blue navy                                200                                                                                  ##STR142##    "             "   blue navy                                201                                                                                  ##STR143##    "             "   blue navy                                202  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                              "             "   blue                                                                           navy                                     203  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)                                                          "             "   blue                                                                           navy                                     204  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (i)                                                          "             "   blue                                                                           navy                                     205  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)                                                          "             "   blue                                                                           navy                                     206  C.sub.3 H.sub.6 OCH.sub.3                                                                     "             "   blue                                                                           navy                                     207  C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                              "             "   blue                                                                           navy                                     208  C.sub.3 H.sub.6 OC.sub.3 H.sub.7 (n)                                                          "             "   blue                                                                           navy                                     209  C.sub.3 H.sub.6 OC.sub.8 H.sub.17 (i)                                                         "             "   blue                                                                           navy                                     210                                                                                  ##STR144##                                                                                    ##STR145##   H   navy                                     211  "              C.sub.3 H.sub.6 OCH.sub.3                                                                    "    "                                       212                                                                                  ##STR146##                                                                                    ##STR147##   "   blue navy                                213                                                                                  ##STR148##    "             "   blue navy                                214                                                                                  ##STR149##    "             "   blue navy                                215                                                                                  ##STR150##    "             "   blue navy                                216  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                              "             "   blue                                                                           navy                                     217  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)                                                          "             "   blue                                                                           navy                                     218  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (i)                                                          "             "   blue                                                                           navy                                     219  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)                                                          "             "   blue                                                                           navy                                     220  C.sub.3 H.sub.6 OCH.sub.3                                                                     "             "   blue                                                                           navy                                     221  C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                              "             "   blue                                                                           navy                                     222  C.sub.3 H.sub.6 OC.sub.3 H.sub.7 (n)                                                          "             "   blue                                                                           navy                                     223  C(CH.sub.3).sub.3                                                                              ##STR151##   "   blue navy                                224  C.sub.6 H.sub.5                                                                                ##STR152##   "   blue navy                                225  C.sub.4 H.sub.9 (n)                                                                            ##STR153##   "   blue navy                                226                                                                                  ##STR154##    C.sub.6 H.sub.5                                                                              "   blue navy                                ______________________________________                                     

We claim:
 1. A benzisothiazolylazo dye of the formula ##STR155## wherein one of R¹ or R² is phenyl substituted by methoxy, and the other R¹ or R² is methoxyethyl, ethoxyethyl, methoxypropyl, ethoxypropyl, --CH(C₂ H₅)--CH₂ OCH₃ or --CH(CH₃)--CH₂ OCH₃.
 2. The dye of claim 1, wherein R¹ is phenyl substituted by methoxy and R² is methoxyethyl.
 3. The dye of claim 1, wherein R¹ is phenyl substituted by methoxy and R² is ethoxyethyl.
 4. The dye of claim 1, wherein R¹ is phenyl substituted by methoxy and R² is methoxypropyl.
 5. The dye of claim 1, wherein R¹ is phenyl substituted by methoxy and R² is ethoxypropyl.
 6. The dye of claim 1, wherein R¹ is phenyl substituted by methoxy and R² is --CH(C₂ H₅)--CH₂ OCH₃.
 7. The dye of claim 1, wherein R¹ is phenyl substituted by methoxy and R² is --CH(CH₃)--CH₂ OCH₃.
 8. The dye of claim 1, wherein R¹ is methoxyethyl and R² is phenyl substituted by methoxy.
 9. The dye of claim 1, wherein R¹ is ethoxyethyl and R² is phenyl substituted by methoxy.
 10. The dye of claim 1, wherein R¹ is methoxypropyl and R² is phenyl substituted by methoxy.
 11. The dye of claim 1, wherein R¹ is ethoxypropyl and R² is phenyl substituted by methoxy.
 12. The dye of claim 1, wherein R¹ is --CH(C₂ H₅)--CH₂ OCH₃ and R² is phenyl substituted by methoxy.
 13. The dye of claim 1, wherein R¹ is --CH(CH₃)--CH₂ OCH₃ and R² is phenyl substituted by methoxy. 